4-{5-[bis(2-chloroethyl)amino]-1-methyl-1H-1,3-benzodiazol-2-yl}butanoic acid hydrate hydrochloride

• ChemBase ID: 154551
• Molecular Formular: C16H24Cl3N3O3
• Molecular Mass: 412.73906
• Monoisotopic Mass: 411.08832468
• SMILES: Cn1c2ccc(cc2nc1CCCC(=O)O)N(CCCl)CCCl.O.Cl
• Canonical SMILES: ClCCN(c1ccc2c(c1)nc(n2C)CCCC(=O)O)CCCl.O.Cl
• InChI: InChI=1S/C16H21Cl2N3O2.ClH.H2O/c1-20-14-6-5-12(21(9-7-17)10-8-18)11-13(14)19-15(20)3-2-4-16(22)23;;/h5-6,11H,2-4,7-10H2,1H3,(H,22,23);1H;1H2
• InChIKey: TWBJYCLUHINEDN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{5-[bis(2-chloroethyl)amino]-1-methyl-1H-1,3-benzodiazol-2-yl}butanoic acid hydrate hydrochloride
• IUPAC Traditional name: bendamustine hydrate hydrochloride
• Synonyms: 1H-Benzimidazole-2-butanoic acid, 5-[bis(2-chloroethyl)amino]-1-methyl monohydrochloride; Treanda; Bendamustine hydrochloride hydrate

Database IDs

• MDL Number: MFCD16879055
• PubChem SID: 162248689
• PubChem CID: 66600935

CALCULATED PROPERTIES

• Acid pKa: 4.3772397
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.7300161
• LogD (pH = 7.4): 0.95016146
• Log P: 1.6649948
• Molar Refractivity: 92.9154 cm^3
• Polarizability: 36.44468 Å^3
• Polar Surface Area: 58.36 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >30 mg/mL
• Apperance: off-white powder

Safety Information

• RTECS: DE1590000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 60-61-22-40
• Safety Statements: 36-37
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H351-H360
• GHS Precautionary statements: P201-P281-P301 + P310-P308 + P313
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H21Cl2N3O2·HCl · xH2O

DETAILS

Sigma Aldrich - B5437

Biochem/physiol Actions
Bendamustine hydrochloride is a DNA-alkylator with a distinct pattern of activity. Bendamustine activates DNA-damage stress response and apoptosis; inhibits mitotic checkpoints; and induces mitotic catastrophe.